Herbicidal sulphonylaminocarbonyl triazolinones having substituents bonded via oxygen

ABSTRACT

Herbicidal sulphonylaminocarbonyltriazolinones having substituents bonded via oxygen of the formula ##STR1## in which R 1  represents hydrogen, amino, or an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aryl, alkylamino, cycloalklamino or dialkylamino radical, 
     R 2  represents an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl or aryl radical, and 
     R 3  represents an optionally substituted alkyl, aralkyl, aryl or heteroaryl radical, 
     and salts thereof, with the exception of the compounds: 
     2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)- 4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one, 
     2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)- 4-cyclopropyl-5-methoxy-2,4-dihydro-3H-1,2,4- triazol-3-one, 
     2-(2-difluoromethoxy-phenylsulphonylaminocarbonyl)- 4-cyclobutyl-5-ethoxy-2,4-dihydro-3H-1,2,4-triazol-3-one, and 
     2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)- 4-ethyl 5-ethoxy-2,4-dihydro 3H-1,2,4-triazol-3-one

This application is a continuation of application Ser. No. 08/048,026, filed Apr. 15, 1993, now abandoned, which is a continuation-in-part of Ser. No. 07/857,025, filed on Mar. 24, 1992, now abandoned.

The invention relates to new sulphonylaminocarbonyltriazolinones having substituents bonded via oxygen, to a plurality of processes and novel intermediates for their preparation, and to their use as herbicides.

It has been disclosed that certain substituted sulphonylaminocarbonyltriazolinones such as, for example, 2-(2-chloro-phenylsulphonylaminocarbonyl)-4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one have herbicidal properties (cf. EP-A 341,489). However, the action of these compounds is not satisfactory in all respects.

Further sulphonylaminocarbonyltriazolinones such as, for example, 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one are the subject of an earlier, but non-prior-published Patent Application (cf. German Patent 3,934,081 dated Dec. 10, 1989).

There have now been found the novel sulphonylaminocarbonyltriazolinones having substituents bonded via oxygen, of the general formula (I) ##STR2## in which R¹ represents hydrogen, amino, or an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aryl, alkylamino, cycloalkylamino, dialkylamino,

R² represents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, and

R³ represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl, heteroaryl,

and salts of compounds of the formula (I), with the exception of 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one (cf. German Patent 3,934,081).

The new sulphonylaminocarbonyltriazolinones having substituents bonded via oxygen, of the general formula (I), are obtained when

(a) Triazolinones of the General Formula (II) ##STR3## in which R¹ and R² have the abovementioned meanings

are reacted with sulphonyl isocyanates of the general formula (III)

    R.sup.3 --SO.sub.2 --N═C═O                         (III)

in which

R³ has the abovementioned meaning,

if appropriate in the presence of a diluent, or when

(b) Triazolinone Derivatives of the General Formula (IV) ##STR4## in which R¹ and R² have the abovementioned meanings and

Z represents halogen, alkoxy, aralkoxy or aryloxy,

are reacted with sulphonamides of the general formula (V)

    R.sup.3 --SO.sub.2--NH.sub.2                               (V)

in which

R³ has the abovementioned meaning,

if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or when

(c) Triazolinones of the General Formula (II) ##STR5## in which R¹ and R² have the abovementioned meanings

are reacted with sulphonamide derivatives of the general formula (VI)

    R.sup.3 --SO.sub.2 --NH--CO--Z                             (VI)

in which

R³ has the abovementioned meaning and

Z represents halogen, alkoxy, aralkoxy or aryloxy,

if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent and, if appropriate, salts are formed, by customary methods, of the compounds of the formula (I) which have been prepared by process (a), (b) or (c).

The new sulphonylaminocarbonyltriazolinones having substituents bonded via oxygen, of the general formula (I), and their salts are distinguished by a powerful herbicidal activity.

Surprisingly, the new compounds of the formula (I) show a considerably better herbicidal action than the known compound 2-(2-chlorophenylsulphonylaminocarbonyl)-4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one, which has a similar structure.

The invention preferably relates to compounds of the formula (I) in which

R¹ represents hydrogen, amino, or represents C₁ -C₆ -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylcarbonyl or C₁ -C₄ -alkoxy-carbonyl, or represents C₃ -C₆ -alkenyl or C₃ -C₆ -alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents C₃ -C₆ -cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or C₁ -C₄ -alkyl, or represents phenyl-C₁ -C₃ -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy and/or C₁ -C₄ -alkoxy-carbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy, fluorine- and/or chlorine-substituted C₁ -C₃ -alkoxy, C₁ -C₄ -alkylthio, fluorine- and/or chlorine-substituted C₁ -C₃ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl and/or C₁ -C₄ -alkoxy-carbonyl, or represents C₁ -C₄ -alkylamino which is optionally substituted by fluorine, cyano, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxy-carbonyl, or represents C₃ -C₆ -cycloalkylamino or di-(C₁ -C₄ -alkyl)-amino,

R² represents C₁ -C₆ -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C₃ -C₆ -cycloalkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxycarbonyl, or represents C₃ -C₆ -alkenyl or C₃ -C₆ -alkinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents C₃ -C₆ -cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or C₁ -C₄ -alkyl, or represents cyclohexenyl, or represents phenyl-C₁ -C₃ -alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy and/or C₁ -C₄ -alkoxy-carbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy, fluorine- and/or chlorine-substituted C₁ -C₃ -alkoxy, C₁ -C₄ -alkylthio, fluorine- and/or chlorine-substituted C₁ -C₃ -alkylthio, C₁ -C₄ -alkyl-sulphinyl, C₁ -C₄ -alkylsulphonyl and/or C₁ -C₄ -alkoxy-carbonyl, and

R³ represents the group ##STR6## in which R⁴ and R⁵ are identical or different and represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C₁ -C₆ -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylamino-carbonyl, di-(C₁ -C₄ -alkyl)amino-carbonyl, hydroxyl, C₁ -C₄ -alkoxy, formyloxy, C₁ -C₄ -alkyl-carbonyloxy, C₁ -C₄ -alkoxycarbonyloxy, C₁ 1∝C₄ -alkylamino-carbonyloxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, di-(C₁ -C₄ -alkyl)-aminosulphonyl, C₃ -C₆ -cycloalkyl or phenyl), or represent C₂ -C₆ -alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl), or represent C₂ -C₆ -alkinyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl), or represent C₁ -C₄ -alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl), or represent C₁ -C₄ -alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl), or represent C₃ -C₆ -alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C₁ -C₄ -alkoxycarbonyl), or represent C₂ -C₆ -alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₃ -alkylthio or C₁ -C₄ -alkoxycarbonyl), C₃ -C₆ -alkinyloxy, C₃ -C₆ -alkinylthio or the radical --S(O)_(p) --R⁶ where

p represents the numbers 1 or 2 and

R⁶ represents C₁ -C₄ -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano or C₁ -C₄ -alkoxy-carbonyl), C₃ -C₆ -alkenyl, C₃ -C₆ -alkinyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkoxy-C₁ -C₄ -alkylamino, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)-amino, phenyl or the radical --NHOR⁷ where

R⁷ represents C₁ -C₁₂ -alkyl (which is optionally substituted by fluorine, chlorine, cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, C₁ -C₄ -alkyl-carbonyl, C₁ -c₄ -alkoxy-carbonyl, C₁ -C₄ -alkylamino-carbonyl or di-(C₁ -C₄ -alkyl)-amino-carbonyl), or represents C₃ -C₆ -alkenyl (which is optionally substituted by fluorine, chlorine or bromine), C₃ -C₆ -alkinyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₂ -alkyl, phenyl-C₁ -C₂ -alkyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxy-carbonyl), or represents benzhydryl, or represents phenyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy, C₁ -C₂ -fluoroalkoxy, C₁ -C₄ -alkylthio, trifluoromethylthio or C₁ -C₄ -alkoxy-carbonyl),

R⁴ and/or R⁵ furthermore represent phenyl or phenoxy, or represent C₁ -C₄ -alkylcarbonylamino, C₁ -C₄ -alkoxy-carbonylamino, C₁ -C₄ -alkylamino-carbonyl-amino, di-(C₁ -C₄ -alkyl)-amino-carbonylamino, or the radical --CO--R⁸ where

R⁸ represents C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₃ -C₆ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylamino, C₁ -C₄ -alkoxyamino, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl-amino or di-(C₁ -C₄ -alkyl)-amino (which are optionally substituted by fluorine and/or chlorine),

R⁴ and/or R⁵ furthermore represent trimethylsilyl, thiazolinyl, C₁ -C₄ -alkylsulphonyloxy, di-(C₁ -C₄ -alkyl)-aminosulphonylamino or the radical --CH═N--R⁹ where

R⁹ represents C₁ -C₆ -alkyl which is optionally substituted by fluorine, chlorine, cyano, carboxyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl, or represents benzyl which is optionally substituted by fluorine or chlorine, or represents C₃ -C₆ -alkenyl or C₃ -C₆ -alkinyl, each of which is optionally substituted by fluorine or chlorine, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, or represents optionally fluorine- and/or chlorine-substituted C₁ -C₆ -alkoxy, C₃ -C₆ -alkenoxy, C₃ -C₆ -alkinoxy or benzyloxy, or represents amino, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)-amino, phenylamino, C₁ -C₄ -alkyl-carbonyl-amino, C₁ -C₄ -alkoxy-carbonylamino or C₁ -C₄ -alkyl-sulphonylamino, or represents phenylsulphonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl,

furthermore

R³ represents the radical ##STR7## where R¹⁰ represents hydrogen or C₁ -C₄ -alkyl,

R¹¹ and R¹² are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), carboxyl, C₁ -C₄ -alkoxy-carbonyl, dimethylaminocarbonyl, C₁ -C₄ -alkylsulphonyl or di-(C₁ -C₄ -alkyl)-aminosulphonyl;

furthermore

R³ represents the radical ##STR8## where R¹³ and R⁴ are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine) or C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine);

furthermore

R³ represents the radical ##STR9## where R¹⁵ and R¹⁶ are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), or represent C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent aminosulphonyl, mono-(C₁ -C₄ -alkyl)-aminosulphonyl, di-(C₁ -C₄ -alkyl)-aminosulphonyl or C₁ -C₄ -alkoxycarbonyl or dimethylaminocarbonyl;

furthermore

R³ represents the radical ##STR10## where R¹⁷ and R¹⁸ are identical or different and represent hydrogen, fluorine, chlorine, bromine, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or bromine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), or represent di-(C₁ -C₄ -alkyl)-aminosulphonyl;

furthermore

R³ represents the radical ##STR11## where R¹⁹ and R²⁰ are identical or different and represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine), di-(C₁ -C₄ -alkyl)-amino-sulphonyl, C₁ -C₄ -alkoxy-carbonyl or dimethylaminocarbonyl, and

A represents oxygen, sulphur or the group N--Z¹, where

Z¹ represents hydrogen, C₁ -C₄ -alkyl (which is optionally substituted by fluorine, chlorine, bromine or cyano), C₃ -C₆ -cycloalkyl, benzyl, phenyl (which is optionally substituted by fluorine, chlorine, bromine or nitro), C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxy-carbonyl or di-(C₁ -C₄ -alkyl)-amino-carbonyl;

furthermore

R³ represents the radical ##STR12## where R²¹ and R²² are identical or different and represent hydrogen, C₁ -C₄ -alkyl, halogen, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkoxy or C₁ -C₄ -halogenoalkoxy,

Y¹ represents sulphur or the group N--R²³ where

R²³ represents hydrogen or C₁ -C₄ -alkyl;

furthermore

R³ represents the radical ##STR13## where R²⁴ represents hydrogen, C₁ -C₄ -alkyl, benzyl, pyridyl, quinolinyl or phenyl,

R²⁵ represents hydrogen, halogen, cyano, nitro, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), dioxolanyl or C₁ -C₄ -alkoxy-carbonyl and

R²⁶ represents hydrogen, halogen or C₁ -C₄ -alkyl;

furthermore

R³ represents one of the groups listed below ##STR14##

The invention furthermore preferably relates to the sodium, potassium, magnesium, calcium, ammonium, C₁ -C₄ -alkyl-ammonium, di-(C₁ -C₄ -alkyl)-ammonium, tri-(C₁ -C₄ -alkyl)-ammonium, C₅ - or C₆ -cycloalkyl-ammonium and di-(C₁ -C₂ -alkyl)-benzyl-ammonium salts of compounds of the formula (I) in which R¹, R² and R³ have the meanings mentioned above as being preferred.

In particular, the invention relates to compounds of the formula (I) in which

R¹ represents hydrogen, amino, C₁ -C₄ -alkyl which is optionally substituted by fluorine, cyano, methoxy or ethoxy, or represents allyl, C₃ -C₆ -cycloalkyl, benzyl, phenyl, C₁ -C₃ -alkylamino, C₃ -C₆ -cycloalkylamino or di-(C₁ -C₃ -alkyl)-amino,

R² represents C₁ -C₄ -alkyl which is optionally substituted by fluorine and/or chlorine, methoxy or ethoxy, or represents C₃ -C₄ -alkenyl which is optionally substituted by fluorine and/or chlorine, or represents C₃ -C₆ -cycloalkyl, or represents benzyl which is optionally substituted by fluorine, chlorine and/or methyl, and

R³ represents the group ##STR15## where R⁴ represents fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-methoxy-ethoxy, C₁ -C₃ -alkylthio, C₁ -C₃ -alkylsulphinyl, C₁ -C₃ -alkylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylaminosulphonyl, methoxyaminosulphonyl, phenyl, phenoxy or C₁ -C₃ -alkoxy-carbonyl and

R⁵ represents hydrogen, fluorine, chlorine or bromine;

furthermore

R³ represents the radical ##STR16## where R¹⁰ represents hydrogen,

R¹¹ represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl and

R¹² represents hydrogen;

furthermore

R³ represents the radical ##STR17## where R represents C₁ -C₄ -alkyl, or represents the radical ##STR18## where R represents C₁ -C₄ -alkyl.

The abovementioned definitions of radicals, in general or mentioned in preferred ranges, can be combined with each other in any desired way, that is to say also between the particular preferred ranges.

Examples of the compounds according to the invention are listed in Table 1 below--cf. also the Preparation Examples.

                                      TABLE 1                                      __________________________________________________________________________     Examples of the compounds of the formula (I)                                    ##STR19##                           (I)                                       R.sup.1   R.sup.2    R.sup.3                                                   __________________________________________________________________________      ##STR20##                                                                               CH.sub.3                                                                                   ##STR21##                                                 ##STR22##                                                                               CH.sub.3                                                                                   ##STR23##                                                CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR24##                                                CH.sub.3  CH.sub.2CHCH.sub.2                                                                         ##STR25##                                                CH.sub.3  CH.sub.3                                                                                   ##STR26##                                                CH.sub.3  CH.sub.3                                                                                   ##STR27##                                                CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR28##                                                CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR29##                                                CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR30##                                                C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                            ##STR31##                                                C.sub.2 H.sub.5                                                                          C.sub.3 H.sub.7                                                                            ##STR32##                                                 ##STR33##                                                                               CH.sub.3                                                                                   ##STR34##                                                 ##STR35##                                                                               C.sub.2 H.sub.5                                                                            ##STR36##                                                 ##STR37##                                                                               CH(CH.sub.3).sub.2                                                                         ##STR38##                                                CH.sub.3  CH(CH.sub.3).sub.2                                                                         ##STR39##                                                CH.sub.3  CH.sub.2CHCH.sub.2                                                                         ##STR40##                                                C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                   ##STR41##                                                C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                            ##STR42##                                                CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR43##                                                C.sub.2 H.sub.5                                                                          C.sub.3 H.sub.7                                                                            ##STR44##                                                CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR45##                                                 ##STR46##                                                                               CH.sub.3                                                                                   ##STR47##                                                 ##STR48##                                                                               C.sub.2 H.sub.5                                                                            ##STR49##                                                 ##STR50##                                                                               CH.sub.3                                                                                   ##STR51##                                                 ##STR52##                                                                               C.sub.2 H.sub.5                                                                            ##STR53##                                                 ##STR54##                                                                               C.sub.3 H.sub.7 -n                                                                         ##STR55##                                                CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR56##                                                CH.sub.3  CH.sub.3                                                                                   ##STR57##                                                CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR58##                                                CH.sub.3  SCH.sub.2CCH                                                                               ##STR59##                                                CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR60##                                                 ##STR61##                                                                               C.sub.2 H.sub.5                                                                            ##STR62##                                                 ##STR63##                                                                               CH.sub.3                                                                                   ##STR64##                                                CH.sub.3  CH.sub.3                                                                                   ##STR65##                                                CH.sub.3  C.sub.3 H.sub.7                                                                            ##STR66##                                                C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                            ##STR67##                                                CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                            ##STR68##                                                CH.sub.2CHCH.sub.2                                                                       CH.sub.3                                                                                   ##STR69##                                                C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                   ##STR70##                                                C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                            ##STR71##                                                C.sub.3 H.sub.7                                                                          CH.sub.2CHCH.sub.2                                                                         ##STR72##                                                CH.sub.3  CH.sub.3                                                                                   ##STR73##                                                 ##STR74##                                                                               C.sub.2 H.sub.5                                                                            ##STR75##                                                 ##STR76##                                                                               C.sub.2 H.sub.5                                                                            ##STR77##                                                C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                            ##STR78##                                                CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR79##                                                CH.sub.3  C.sub.3 H.sub.7                                                                            ##STR80##                                                C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                   ##STR81##                                                C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                   ##STR82##                                                C.sub.3 H.sub.7                                                                          C.sub.2 H.sub.5                                                                            ##STR83##                                                C.sub.3 H.sub.7                                                                          C.sub.2 H.sub.5                                                                            ##STR84##                                                CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR85##                                                CH.sub.3  CH.sub.3                                                                                   ##STR86##                                                N(CH.sub.3).sub.2                                                                        CH.sub.3                                                                                   ##STR87##                                                CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR88##                                                C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                            ##STR89##                                                 ##STR90##                                                                               CH.sub.3                                                                                   ##STR91##                                                CH.sub.3  C.sub.2 H.sub.5                                                                            ##STR92##                                                N(CH.sub.3).sub.2                                                                        CH.sub.3                                                                                   ##STR93##                                                __________________________________________________________________________

If, for example, 2,6-difluoro-phenylsulphonyl isocyanate and 5-ethoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting substances, the course of the reaction in process (a) according to the invention can be outlined by the following equation: ##STR94##

If, for example, 2-methylthio-benzenesulphonamide and 2-chlorocarbonyl-4-dimethylamino-5-propyloxy-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting substances, the course of the reaction in process (b) according to the invention can be outlined by the following equation: ##STR95##

If, for example, N-methoxycarbonyl-2-methoxy-benzenesulphonamide and 5-methoxy-4-difluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one are used as starting substances, the course of the reaction in process (c) according to the invention can be outlined by the following equation: ##STR96##

Formula (II) provides a general definition of the triazolinones to be used as starting substances in processes (a) and (c) according to the invention for the preparation of compounds of the formula (I).

In formula (II), R¹ and R² preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or particularly preferred, for R¹ and R².

Examples of the starting substances of the formula (II) are listed in Table 2 below.

                  TABLE 2                                                          ______________________________________                                         Examples of the starting substances of the                                     formula (II)                                                                    ##STR97##                    (II)                                             R.sup.1          R.sup.2                                                       ______________________________________                                         H                CH.sub.3                                                      CH.sub.3         CH.sub.3                                                      C.sub.2 H.sub.5  CH.sub.3                                                      C.sub.3 H.sub.7  CH.sub.3                                                      CH(CH.sub.3).sub.2                                                                              CH.sub.3                                                      C.sub.4 H.sub.9  CH.sub.3                                                       ##STR98##       CH.sub.3                                                      CH.sub.3         C.sub.2 H.sub.5                                               CH.sub.3         C.sub.3 H.sub.7                                               CH.sub.3         CH(CH.sub.3).sub.2                                            CH.sub.3         CH.sub.2CHCH.sub.2                                            CH.sub.3                                                                                         ##STR99##                                                    CH.sub.3         CH.sub.2CCH                                                   C.sub.2 H.sub.5  C.sub.2 H.sub.5                                               C.sub.3 H.sub.7  C.sub.2 H.sub.5                                                ##STR100##      C.sub.2 H.sub.5                                               CH.sub.2CHCH.sub.2                                                                              C.sub.2 H.sub.5                                               CH.sub.2CHBrCH.sub.2 Br                                                                         C.sub.2 H.sub.5                                                ##STR101##      C.sub.3 H.sub.7                                                ##STR102##      CH.sub.2CHCH.sub.2                                             ##STR103##      CH(CH.sub.3).sub.2                                            C.sub.2 H.sub.5  CH(CH.sub.3).sub.2                                            C.sub.3 H.sub.7  CH(CH.sub.3).sub.2                                            CH.sub.2CHCH.sub.2                                                                              C.sub.3 H.sub.7                                               C.sub.2 H.sub.5  C.sub.3 H.sub.7                                               C.sub.2 H.sub.5  CH.sub.2CCH                                                   C.sub.3 H.sub.7  C.sub.3 H.sub.7                                               ______________________________________                                    

Some of the starting substances of the formula (II) are the subject of an earlier, but non-prior-published, Patent Application (cf. German Patent 4,030,063, dated 22 Sep. 1990).

The compounds of the general formula (II) in which R¹ has the abovementioned meaning and R² represents in each case optionally substituted cycloalkyl, cycloalkenyl, aralkyl or aryl, are new and a subject of the present patent application.

The compounds of the formula (II) are obtained when hydrazinoformic esters of the general formula (VII)

    H.sub.2 N--NH--CO--O--R.sup.4                              (VII)

in which

R⁴ has the abovementioned meaning

are reacted with alkyliminocarbonic diesters of the general formula (VIII) ##STR104## in which

R¹ and R² have the abovementioned meaning, if appropriate in the presence of a diluent such as, for example, methanol, at temperatures between 0° C. and 50° C., and the compounds formed in this process, of the general formula (IX) ##STR105## in which R¹, R² and R⁴ have the abovementioned meaning,

are, if appropriate, isolated by customary methods and heated to temperatures between 50° C. and 150° C., if appropriate in the presence of a diluent such as, for example, toluene, xylene or o-dichlorobenzene (cf. Preparation Examples).

The starting substances of the formulae (VII) and (VIII) are known chemicals.

The intermediates of the formula (IX) are new compounds.

Formula (III) provides a general definition of the sulphonyl isocyanates furthermore to be used as starting substances in process (a) according to the invention for the preparation of compounds of the formula (I).

In formula (III), R³ preferably, or in particular, has that meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or particularly preferred, for R³.

Examples of the starting substances of the formula (III) which may be mentioned are: 2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2-trifluoromethyl-, 2-difluoro-methoxy-, 2-trifluoro-methoxy-, 2-methylthio-, 2-ethylthio-, 2-propylthio-, 2-methylsulphinyl-, 2-methylsulphonyl-, 2-dimethylaminosulphonyl-, 2-diethylaminosulphonyl-, 2-(N-methoxy-N-methyl)-aminosulphonyl-, 2-phenyl-, 2-phenoxy-, 2-methoxycarbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbonyl- and 2-isopropoxycarbonyl-phenylsulphonyl isocyanate, 2-fluoro-, 2-chloro-, 2-difluoromethoxy-, 2-trifluoro-methoxy-, 2-methoxycarbonyl- and 2-ethoxycarbonyl-benzylsulphonyl isocyanate, 2-methoxycarbonyl-3-thienyl-sulphonyl isocyanate, 4-methoxycarbonyl- and 4-ethoxy-carbonyl-1-methyl-pyrazol-5-yl-sulphonyl isocyanate.

The sulphonyl isocyanates of the formula (III) are known and/or can be prepared by processes known per se (cf. U.S. Pat. Nos. 4,127,405, 4,169,719, 4,371,391; EP-A 7,687, 13,480, 21,641, 23,141, 23,422, 30,139, 35,893, 44,808, 44,809, 48,143, 51,466, 64,322, 70,041, 173,312).

Process (a) according to the invention for the preparation of the new compounds of the formula (I) is preferably carried out using diluents. Diluents which are suitable for this purpose are virtually all inert organic solvents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroine, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, esters such as methyl acetate and ethyl acetate, nitriles such as, for example, acetonitrile and propionitrile, amides such as, for example, dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and also dimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphoric triamide.

When carrying out process (a) according to the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temperatures between 0° C. and 150° C., preferably at temperatures between 10° C. and 80° C.

In general, process (a) according to the invention is carried out under atmospheric pressure.

For carrying out process (a) according to the invention, between 1 and 3 moles, preferably between 1 and 2 moles, of sulphonyl isocyanate of the formula (III) are generally employed per mole or triazolinone of the formula (II).

The reactants can be combined in any desired sequence. The reaction mixture is stirred until the reaction is complete and the product is isolated by filtration with suction. In another processing variant, the mixture is concentrated, and the crude product which remains in the residue is brought to crystallisation with a suitable solvent such as, for example, diethyl ether. The product of the formula (I) which is obtained in this way in crystalline form is isolated by filtration with suction.

Formula (IV) provides a general definition of the triazolinone derivatives to be used as starting substances in process (b) according to the invention for the preparation of compounds of the formula (I).

In formula (IV), R¹ and R² preferably, or in particular, have those meanings which have already been mentioned above in connection with description of the compounds of the formula (I) according to the invention as being preferred, or particularly preferred, for R¹ and R² and

Z preferably represents chlorine, C₁ -C₄ -alkoxy, benzyloxy or phenoxy, in particular methoxy or phenoxy.

Examples of the starting substances of the formula (IV) which are possible are the compounds of the formula (IV) which are to be prepared from the compounds of the formula (II) listed in Table 2 and phosgene, methyl chloroformate, benzyl chloroformate, phenyl chloroformate or diphenyl carbonate.

The starting substances of the formula (IV) were hitherto unknown.

The new triazolinone derivatives of the formula (IV) are obtained when triazolinones of the general formula (II) ##STR106## which R¹ and R² have the abovementioned meanings

are reacted with carbonic acid derivatives of the general formula (X)

    Z--CO--Z.sup.1                                             (X)

in which

Z has the abovementioned meaning and

Z¹ represents a leaving group such as chlorine, methoxy, benzyloxy or phenoxy,

if appropriate in the presence of a diluent such as, for example, tetrahydrofuran, and, if appropriate, in the presence of an acid acceptor such as, for example, sodium hydride or potassium tert-butylate, at temperatures between -20° C. and +100° C.

Formula (V) provides a general definition of the sulphonamides furthermore to be used as starting substances in process (b) according to the invention for the preparation of compounds of the formula (I).

In formula (V), R³ preferably, or in particular, has that meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as being preferred, or particularly preferred, for R³.

The following may be mentioned as examples of the starting substances of the formula (V): 2-fluoro-, 2-chloro-, 2-bromo-, 2-methyl-, 2-methoxy-, 2-trifluoromethyl-, 2-difluoro-methoxy-, 2-trifluoro-methoxy-, 2-methylthio-, 2-ethylthio-, 2-propylthio-, 2-methylsulphinyl-, 2-methylsulphonyl-, 2-dimethylamino-sulphonyl-, 2-diethylaminosulphonyl-, 2-(N-methoxy-N-methyl)-aminosulphonyl-, 2-phenyl-, 2-phenoxy-, 2-methoxycarbonyl-, 2-ethoxycarbonyl-, 2-propoxycarbonyl and 2-isopropoxycarbonyl-benzenesulphonamide, 2-fluoro-, 2-chloro-, 2-difluoromethoxy-, 2-trifluoromethoxy-, 2-methoxycarbonyl- and 2-ethoxycarbonyl-phenylmethanesulphonamide, 2-methoxycarbonyl-3-thiophenesulphonamide, 4-methoxycarbonyl- and 4-ethoxycarbonyl-1-methyl-pyrazole-5-sulphonamide.

The sulphonamides of the formula (V) are known and/or can be prepared by processes known per se (cf. U.S. Pat. No. 4,127,405, 4,169,719, 4,371,391; EP-A 7,687, 13,480, 21,641, 23,141, 23,422, 30,139, 35,893, 44,808, 44,809, 48,143, 51,466, 64,322, 70,041, 173,312).

Process (b) according to the invention for the preparation of the new compounds of the formula (I) is preferably carried out using diluents. Diluents which are suitable for this purpose are virtually all inert organic solvents as have been indicated, for example, above in the case of process (a) according to the invention.

Acid acceptors which can be employed in process (b) according to the invention are all acid-binding agents which can customarily be employed for reactions of this type. The following are preferably suitable: alkali metal hydroxides such as, for example, sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as, for example, calcium hydroxide, alkali metal carbonates and alkali metal alcoholates such as sodium carbonate, potassium carbonate, sodium tert-butylate and potassium tert-butylate, furthermore aliphatic, aromatic or heterocyclic amines, for example triethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine, pyridine, 1,5-diazabicyclo-[4.3.0]-non-5-ene (DBN), 1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU) and 1,4-diazabicyclo[2.2.2]-octane (DABCO).

When carrying out process (b) according to the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temperatures between 0° C. and 100° C., preferably at temperatures between 10° C. and 60° C.

Process (b) according to the invention is generally carried out under atmospheric pressure. However, it can also be carried out under increased or reduced pressure.

For carrying out process (b) according to the invention, the starting substances required in each case are generally employed in approximately equimolar amounts. However, it is also possible to use one of the two components employed in each case in a larger excess. In general, the reactions are carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the particular temperature required. Working-up in process (b) according to the invention is carried out in each case by customary methods.

The triazolinones of the formula (II) to be used as starting substances in process (c) according to the invention for the preparation of compounds of the formula (I) have already been described as starting substances for process (a) according to the invention.

Formula (VI) provides a general definition of the sulphonamide derivatives furthermore to be used as starting substances in process (c) according to the invention for the preparation of compounds of the formula (I).

In formula (VI), R³ and Z preferably, or in particular, have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) or (IV) according to the invention as being preferred, or particularly preferred, for R³ and Z.

Process (c) according to the invention is preferably carried out using diluents. Solvents which are suitable for this purpose are the same organic solvents as have been mentioned above in connection with the description of process (a) according to the invention.

If appropriate, process (c) is carried out in the presence of an acid acceptor. Acid-binding agents which are suitable for this purpose are the same as have been mentioned above in connection with the description of process (b) according to the invention.

When carrying out process (c), the reaction temperatures can vary within a substantial range. In general, the process is carried out at temperatures between 0° C. and 100° C., preferably at temperatures between 10° C. and 60° C.

In general, process (c) according to the invention is carried out under atmospheric pressure. However, the process can also be carried out under increased or reduced pressure.

For carrying out process (c) according to the invention, the starting substances required in each case are generally employed in approximately equimolar amounts. However, it is also possible to use one of the two components employed in each case in a larger excess. The reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the particular temperature required. Working-up is carried out in process (c) according to the invention in each case by customary methods.

To convert the compounds of the formula (I) into salts, they are stirred with suitable salt formers such as, for example, sodium hydroxide, sodium methylate, sodium ethylate, potassium hydroxide, potassium methylate or potassium ethylate, ammonia, isopropylamine, dibutylamine or triethylamine, in suitable diluents such as, for example, water, methanol or ethanol. The salts can be isolated in the form of crystalline products, if appropriate after concentration.

The active compounds according to the invention can be used as defoliants, desiccants, agents for destroying broad-leaved plants and, especially, as weed-killers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in connection with the following plants:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeurn, Avena, Secale, Sorghum, Panicurn, Saccharum, Ananas, Asparagus and Allium.

However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.

The compounds are suitable, depending on the concentration, for the total combating of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for combating weeds in perennial cultures, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, on lawns, turf and pasture-land, and for the selective combating of weeds in annual cultures.

Some of the compounds of the formula (I) according to the invention are suitable for total or semi-total weed control, some for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon cultures, both pre-emergence and post-emergence.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents.

In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. As liquid solvents, there are suitable in the main: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water.

As solid carriers there are suitable: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates, as solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; as emulsifying and/or foam-forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as albumen hydrolysis products; as dispersing agents there are suitable: for example lignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.

For combating weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.

Suitable herbicides for the mixtures are known herbicides, such as, for example, 1-amino-6-ethylthio-3-(2,2-dimethylpropyl)-1,3,5-triazine-2,4-(1H,3H)-dione (AMETHYDIONE) or N-(2-benzothiazolyl)-N,N'-dimethyl-urea (METABENZTHIAZURON) for combating weeds in cereals; 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one (METAMITRON) for combating weeds in sugar beet and 4-amino-6-(1,1-dimethylethyl)-3-methylthio-1,2,4-triazin-5(4H)-one (METRIBUZIN) for combating weeds in soya beans; furthermore also 2,4-dichlorophenoxyacetic acid (2,4-D); 4-(2,4-dichlorophenoxy)-butyric acid (2,4-DB); 2,4-dichlorophenoxypropionic acid (2,4-DP); 5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitro-benzoic acid (ACIFLUORFEN); N-(methoxy-methyl)-2,6-diethyl-chloroacetanilide (ALACHLOR); methyl-6,6-dimethyl-2,4-dioxo-3-[1-(2-propenyloxyamino)-butylidene]-cyclohexanecarboxylic acid (ALLOXYDIM); 4-amino-benzenesulphonyl-methyl carbamate (ASULAM); 2-chloro-4-ethylamino-6-isopropylamino- 1,3,5-triazine (ATRAZINE); methyl 2-[[[[[(4,6-dimethoxypyrimidin-2-yl)-amino]-carbonyl]-amino]-sulphonyl]methyl]-benzoate (BENSULFURON); 3-isopropyl-2,1,3-benzothiadiazin-4-one 2,2-dioxide (BENTAZONE); methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate (BIFENOX); 3,5-dibromo-4-hydroxy-benzonitrile; (BROMOXYNIL); N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)-acetamide (BUTACHLOR); 5-amino-4-chloro-2-phenyl-2,3-dihydro-3-oxy-pyridazine (CHLORIDAZON); ethyl 2-{[(4-chloro-6-methoxy-2-pyrimidinyl)-aminocarbonyl]-aminosulphonyl}-benzoate (CHLORIMURON); N-(3-chlorophenyl)-isopropyl carbamate (CHLOROPROPHAM); 2-chloro-N-{[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl}-benzenesulphonamide (CHLORSULFURON); N,N-dimethyl-N'-(3-chloro-4-methyl-phenyl)-urea (CHLORTOLURON); exo-1-methyl-4-(1-methyl-ethyl)-2-(2-methylphenyl-methoxy)-7-oxabicyclo-(2,2,1)-heptane (CINMETHYLIN); 3,6-dichloro-2-pyridinecarboxylic acid (CLOPYRALID); 2-chloro-4-ethylamino-6-(3-cyanopropylamino)-1,3,5-triazine (CYANAZINE); N,S-diethyl N-cyclohexyl-thiocarbamate (CYCLOATE); 2-[1-(ethoximino)butyl]-3-hydroxy-5-[tetrahydro-(2H)-thiopyran-3-yl]-2-cyclohexen-1-one (CYCLOXYDIM); 2-[4-(2,4-dichlorophenoxy)-phenoxy]-propionic acid, its methyl ester or its ethyl ester (DICLOFOP); 2-[(2-chlorophenyl)-methyl]-4,4-dimethylisoxazolidin-3-one (DIMETHAZONE); S-ethyl N,N-di-n-propyl-thiocarbamidate (EPTAME); 4-amino-6-t-butyl-3-ethylthio-1,2,4-triazin-5(4H)-one (ETHIOZIN); 2-{4-[(6-chloro-2-benzoxazolyl)-oxy]-phenoxy}-propanoic acid, its methyl ester or its ethyl ester (FENOXAPROP); 2-[4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy]-propanoic acid or its butyl ester (FLUAZIFOP); N,N-dimethyl-N'-(3-trifluoromethylphenyl)-urea (FLUOMETURON); 1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)-4-pyridone (FLURIDONE); [(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)-oxy]-acetic acid or its 1-methylheptyl ester (FLUROXYPYR); 5-(2-chloro-4-trifluoromethyl-phenoxy)-N-methylsulphonyl-2-nitrobenzamide (FOMESAFEN); N-phosphonomethyl-glycine (GLYPHOSATE); 2-{4-[(3-chloro-5-(trifluoromethyl)-2-pyridinyl)-oxy]-phenoxy}-propanoic acid or its ethyl ester (HALOXYFOP); 3-cyclohexyl-6-dimethylamino-1-methyl-1,3,5-triazine-2,4-dione (HEXAZINONE); methyl2-[4,5-dihydro-4-methyl-4-(1-methyl-ethyl)-5-oxo-1H-imidazol-2-yl]-4(5)-methylbenzoate (IMAZAMETHABENZ); 2-(4,5-dihydro-4-methyl-4-isopropyl-5-oxo-1H-imidazol-2-yl)-pyridine-3-carboxylic acid (IMAZAPYR); 2-[5-methyl-5-(1-methylethyl)-4-oxo-2-imidazolin-2-yl]-3-quinolinecarboxylic acid (IMAZAQUIN); 2-[4,5-dihydro-4-methyl-4-isopropyl-5-oxo-(1H)-imidazol-2-yl]-5-ethylpyridin-3-carboxylic acid (IMAZETHAPYR); 3,5-diiodo-4-hydroxybenzonitrile (IOXYNIL); N,N-dimethyl-N'-(4-isopropylphenyl)-urea (ISOPROTURON); 2-ethoxy-1-methyl-2-oxo-ethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]- 2-nitrobenzoate (LACTOFEN); (2-methyl-4-chlorophenoxy)-acetic acid (MCPA); (4-chloro-2-methylphenoxy)propionic acid (MCPP); N-methyl-2-(1,3-benzothiazol-2-yloxy)-acetanilide (MEFENACET); 2-chloro-N-(2,6-dimethylphenyl)-N-[(1H)-pyrazol-1-yl-methyl]-acetamide (METAZACHLOR); 2-ethyl-6-methyl-N-(1-methyl-2-methoxy-ethyl)-chloroacetanilide (METOLACHLOR); 2-{[[((4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino)-carbonyl]-amino]-sulphonyl} -benzoic acid or its methyl ester (METSULFURON); S-ethyl N,N-hexamethylene-thiocarbamate (MOLINATE); 1-(3-trifluoromethyl-phenyl)-4-methylamino-5-chloro-6-pyridazone (NORFLURAZON); 4-(di-n-propylamino)-3,5-dinitrobenzenesulphonamide (ORYZALIN); 2-chloro-4-trifluoromethylphenyl 3-ethoxy-4-nitro-phenyl ether (OXYFLUORFEN); N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitroaniline (PENDIMETHALIN); 3-(ethoxycarbonylaminophenyl) N-(3'-methylphenyl)-carbamate (PHENMEDIPHAM); 4-amino-3,5,6-trichloropyridine-2-carboxylic acid (PICLORAM); α-chloro-2',6'-diethyl-N-(2-propoxyethyl)-acetanilide (PRETILACHLOR); 2-chloro-N-isopropylacetanilide (PROPACHLOR); isopropyl-N-phenyl-carbamate (PROPHAM); O-(6-chloro-3-phenyl-pyridazin-4-yl) S-octyl thiocarbonate (PYRIDATE); ethyl 2-[4-(6-chloro-quinoxalin-2-yl-oxy)-phenoxy]-propionate (QUIZALOFOP-ETHYL); 2-[1-(ethoxamino)-butylidene]-5-(2-ethylthiopropyl)-1,3-cyclohexadione (SETHOXYDIM); 2-chloro-4,6-bis-(ethylamino)-1,3,5-triazine (SIMAZINE); 2,4-bis-[N-ethylamino]-6-methylthio-1,3,5-triazine (SIMETRYNE); methyl 2-{[(4,6-dimethyl-2-pyrimidinyl)-aminocarbonyl]-aminosulphonyl}-benzoate (SULFOMETURON); 4-ethylamino-2-t-butylamino-6-methylthio-s-triazine (TERBUTRYNE); methyl 3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl]-amino]-sulphonyl]-thiophene-2-carboxylate (THIAMETURON); S-[(4-chlorophenyl)-methyl] N,N-diethylthiocarbamate (THIOBENCARB); S-(2,3,3-trichloroallyl) N,N-diisopropylthiocarbamate (TRIALLATE); 2,6-dinitro-4-trifluoromethyl-N,N-dipropylaniline (TRIFLURALIN).

Surprisingly, some mixtures also show a synergistic action.

Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomising or scattering.

The active compounds according to the invention can be applied either before or after emergence of the plants.

They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.

The preparation and use of the active compounds according to the invention can be seen from the following examples.

PREPARATION EXAMPLES Example 1 ##STR107## (Process (a))

A mixture of 2.0 g (10.5 mmol) of 4-methyl-5-phenoxy-2,4-dihydro-3H-1,2,4-triazol-3-one, 3.5 g (14.5 mmol) of 2-methoxycarbonyl-phenylsulphonyl isocyanate and 60 ml of acetonitrile is stirred for 6 hours at 20° C. and subsequently concentrated under a water pump vacuum. The residue is stirred with diethyl ether and the product which has precipitated in crystalline form is isolated by filtration with suction.

4.1 g (90% of theory) of 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-phenoxy-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 161° C. are obtained.

Other examples of compounds of the formula (I) which can be prepared-analogously to Example 1 and following the general description of the preparation processes according to the invention are those listed in Table 3 below.

                                      TABLE 3                                      __________________________________________________________________________      ##STR108##                                  (I)                               Preparation Examples of the compounds of the                                   formula (I)                                                                    Example                                 Melting                                No.  R.sup.1   R.sup.2     R.sup.3      point (°C.)                     __________________________________________________________________________           ##STR109##                                                                              C.sub.2 H.sub.5                                                                             ##STR110##  183                                    3    CH.sub.3                                                                                  ##STR111##                                                                                 ##STR112##  190                                    4    CH.sub.3  C.sub.3 H.sub.7                                                                             ##STR113##  120                                    5    CH.sub.3  C.sub.3 H.sub.7                                                                             ##STR114##  134                                    6    CH.sub.3  C.sub.3 H.sub.7                                                                             ##STR115##  122                                    7    CH.sub.3  C.sub.3 H.sub.7                                                                             ##STR116##  125                                    8    CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR117##  166-167                                9    CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR118##  131-132                                10   CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR119##  147-148                                11   CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR120##  186-187                                12   CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR121##  125-126                                13   CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR122##  123-124                                14   CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR123##  188-189                                15   CH.sub.3  C.sub. 2 H.sub.5                                                                            ##STR124##  175-176                                16   CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR125##  152-153                                17   CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR126##  172-173                                18   CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR127##  147-148                                19   CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR128##  183-184                                20   CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR129##  178-183                                21   CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR130##  155-156                                22   CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR131##  162-163                                23   CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR132##  146-147                                24   C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                    ##STR133##  129-130                                25   C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                    ##STR134##  150-151                                26   C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                    ##STR135##  130-131                                27   C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                    ##STR136##  135-136                                28   C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                    ##STR137##  126-127                                29   C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                    ##STR138##  116-117                                30   C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                    ##STR139##  129-130                                31   C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                    ##STR140##  156-157                                32   C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                    ##STR141##  117-118                                33   C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                    ##STR142##  139-140                                34   C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                    ##STR143##  115-116                                35   C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                    ##STR144##  183-184                                36   C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                    ##STR145##  130-131                                37   C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                    ##STR146##  108-109                                38   C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                    ##STR147##  122-123                                39   C.sub.3 H.sub.7                                                                          CH.sub.3                                                                                    ##STR148##  128-129                                40   CH.sub.3  C.sub.4 H.sub.9                                                                             ##STR149##  76                                     41   CH.sub.3  C.sub.4 H.sub.9                                                                             ##STR150##  197                                    42   CH.sub.3  C.sub.4 H.sub.9                                                                             ##STR151##  153                                    43   CH.sub.3  C.sub.4 H.sub.9                                                                             ##STR152##  105                                    44   CH.sub.3  C.sub.4 H.sub.9                                                                             ##STR153##  81                                     45   CH.sub.3  C.sub.4 H.sub.9                                                                             ##STR154##  137                                    46   CH.sub.3  C.sub.4 H.sub.9                                                                             ##STR155##  148                                    47   CH.sub.3  C.sub.4 H.sub.9                                                                             ##STR156##  114                                    48   CH.sub.3  C.sub.4 H.sub.9                                                                             ##STR157##  147                                    49   CH.sub.3  C.sub.4 H.sub.9                                                                             ##STR158##  139                                    50                                                                                   ##STR159##                                                                              C.sub.2 H.sub.5                                                                             ##STR160##  114                                    51                                                                                   ##STR161##                                                                              C.sub.2 H.sub.5                                                                             ##STR162##  135                                    52                                                                                   ##STR163##                                                                              C.sub.2 H.sub.5                                                                             ##STR164##  108                                    53   CH.sub.3                                                                                  ##STR165##                                                                                 ##STR166##  209                                    54   CH.sub.3                                                                                  ##STR167##                                                                                 ##STR168##  191                                    55   CH.sub.3                                                                                  ##STR169##                                                                                 ##STR170##  207                                    56   CH.sub.3  CH.sub.3                                                                                    ##STR171##  154                                    57   CH.sub.3  CH.sub.3                                                                                    ##STR172##  187                                    58   CH.sub.3  CH.sub.3                                                                                    ##STR173##  179                                    59   CH.sub.2CHCH.sub.2                                                                       CH.sub.3                                                                                    ##STR174##  124                                    60   CH.sub.2CHCH.sub.2                                                                       CH.sub.3                                                                                    ##STR175##  153                                    61   CH.sub.2CHCH.sub.2                                                                       CH.sub.3                                                                                    ##STR176##  150                                    62   CH.sub.2CHCH.sub.2                                                                       CH.sub.3                                                                                    ##STR177##  103                                    63   CH.sub.2CHCH.sub.2                                                                       CH.sub.3                                                                                    ##STR178##  130                                    64   CH.sub.3  CH.sub.3                                                                                    ##STR179##  196                                    65   CH.sub.3  CH.sub.3                                                                                    ##STR180##  136                                    66   CH.sub.2CHCH.sub.2                                                                       CH.sub.3                                                                                    ##STR181##  130                                    67   CH.sub.3                                                                                  ##STR182##                                                                                 ##STR183##  211                                    68   CH.sub.3                                                                                  ##STR184##                                                                                 ##STR185##  179                                    69   CH.sub.3  CH.sub.3                                                                                    ##STR186##  171                                    70   CH.sub.2CHCH.sub.2                                                                       CH.sub.3                                                                                    ##STR187##  115                                    71   CH.sub.3                                                                                  ##STR188##                                                                                 ##STR189##  162                                    72   CH.sub.3  C.sub.3 H.sub.7                                                                             ##STR190##  141                                    73   CH.sub.3  CH.sub.3                                                                                    ##STR191##  148                                    74   CH.sub.3                                                                                  ##STR192##                                                                                 ##STR193##  174                                    75   CH.sub.2CHCH.sub.2                                                                       CH.sub.3                                                                                    ##STR194##  138                                    76                                                                                   ##STR195##                                                                              CH.sub.3                                                                                    ##STR196##  148                                    77                                                                                   ##STR197##                                                                              CH.sub.3                                                                                    ##STR198##  150                                    78   CH.sub.2CHCH.sub.2                                                                       CH.sub.3                                                                                    ##STR199##  125                                    79   CH.sub.3  CH.sub.3                                                                                    ##STR200##  145                                    80   C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                    ##STR201##  153-154                                81   C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                    ##STR202##  151-152                                82   C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                    ##STR203##  167-168                                83   C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                    ##STR204##  155-156                                84   C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                    ##STR205##  174-175                                85   C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                    ##STR206##  140-141                                86   C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                    ##STR207##  160                                    87   C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                    ##STR208##  146-147                                88   C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                    ##STR209##  156-157                                89   C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                    ##STR210##  125-126                                90   C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                    ##STR211##  137-138                                91   C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                    ##STR212##  203-204                                92   CH.sub.3  C.sub.4 H.sub.9                                                                             ##STR213##  118-119                                93   CH.sub.3  C.sub.4 H.sub.9                                                                             ##STR214##  146-147                                94   CH.sub.3  C.sub.4 H.sub.9                                                                             ##STR215##  110-111                                95   CH.sub.3  C.sub. 4 H.sub.9                                                                            ##STR216##  123-124                                96                                                                                   ##STR217##                                                                              C.sub.2 H.sub.5                                                                             ##STR218##  152-153                                97                                                                                   ##STR219##                                                                              C.sub.2 H.sub.5                                                                             ##STR220##  116-117                                98                                                                                   ##STR221##                                                                              C.sub.2 H.sub.5                                                                             ##STR222##  145-146                                99                                                                                   ##STR223##                                                                              C.sub.2 H.sub.5                                                                             ##STR224##  132-133                                100                                                                                  ##STR225##                                                                              C.sub.2 H.sub.5                                                                             ##STR226##  88-89                                  101                                                                                  ##STR227##                                                                              C.sub.2 H.sub.5                                                                             ##STR228##  128-129                                102                                                                                  ##STR229##                                                                              C.sub.2 H.sub.5                                                                             ##STR230##  79-77                                  103  CH.sub.2CH CH.sub.2                                                                      C.sub.2 H.sub.5                                                                             ##STR231##  114-115                                104  CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR232##  104-106                                105  CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR233##  85-86                                  106  CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR234##  121-122                                107  CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR235##  107-108                                108  CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR236##  123-124                                109  CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR237##  131-132                                110  CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR238##  118-119                                111  CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR239##  110-111                                112  CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR240##  123-124                                113  CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR241##  103-104                                114  CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR242##  >250                                   115  CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR243##  114-115                                116  CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR244##  122-123                                117  CH(CH.sub.3).sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR245##  188-190                                118  CH(CH.sub.3).sub. 2                                                                      C.sub.2 H.sub.5                                                                             ##STR246##  230-231                                119  CH(CH.sub.3).sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR247##  129-130                                120  CH(CH.sub.3).sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR248##  207 Decomposes                         121  CH(CH.sub.3).sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR249##  113-114                                122  CH(CH.sub.3).sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR250##  195-200                                123  CH(CH.sub.3).sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR251##  133-134                                124  CH(CH.sub.3).sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR252##  139-140                                125  CH(CH.sub.3).sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR253##  105-106                                126  CH(CH.sub.3).sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR254##  123-124                                127  (CH.sub.2).sub.3OCH.sub.3                                                                CH.sub.3                                                                                    ##STR255##  112-114                                128  (CH.sub.2).sub.3OCH.sub.3                                                                CH.sub.3                                                                                    ##STR256##  92-95                                  129  (CH.sub.2).sub.3OCH.sub.3                                                                CH.sub.3                                                                                    ##STR257##  126-127                                130  (CH.sub.2).sub.3OCH.sub.3                                                                CH.sub.3                                                                                    ##STR258##  115-116                                131  (CH.sub.2).sub.3OCH.sub.3                                                                CH.sub.3                                                                                    ##STR259##  112-113                                132  (CH.sub.2).sub.3OCH.sub.3                                                                CH.sub.3                                                                                    ##STR260##  81-82                                  133  (CH.sub.2).sub.3OCH.sub.3                                                                CH.sub.3                                                                                    ##STR261##  104-105                                134  (CH.sub.2).sub.3OCH.sub.3                                                                CH.sub.3                                                                                    ##STR262##  113-114                                135  (CH.sub.2).sub.3OCH.sub.3                                                                CH.sub.3                                                                                    ##STR263##  91-92                                  136  n-C.sub.3 H.sub.7                                                                        C.sub.2 H.sub.5                                                                             ##STR264##  108 Decomposes                         137  n-C.sub.3 H.sub.7                                                                        C.sub.2 H.sub.5                                                                             ##STR265##  212-213                                138  n-C.sub.3 H.sub.7                                                                        C.sub.2 H.sub.5                                                                             ##STR266##  106-107                                139  n-C.sub.3 H.sub.7                                                                        C.sub.2 H.sub.5                                                                             ##STR267##  127-128                                140  n-C.sub.3 H.sub.7                                                                        C.sub.2 H.sub.5                                                                             ##STR268##  95 (Zers.)                             141  n-C.sub.3 H.sub.7                                                                        C.sub.2 H.sub.5                                                                             ##STR269##  132-135                                142  n-C.sub.3 H.sub.7                                                                        C.sub.2 H.sub.5                                                                             ##STR270##  138-140                                143  n-C.sub.3 H.sub.7                                                                        C.sub.2 H.sub.5                                                                             ##STR271##  87-88                                  144  n-C.sub.3 H.sub.7                                                                        C.sub.2 H.sub.5                                                                             ##STR272##  108-109                                145  n-C.sub.3 H.sub.7                                                                        C.sub.2 H.sub.5                                                                             ##STR273##  154-157                                146  n-C.sub.3 H.sub.7                                                                        C.sub.2 H.sub.5                                                                             ##STR274##  130-133                                147  CH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                    ##STR275##  150-151                                148  CH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                    ##STR276##  160-161                                149  CH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                    ##STR277##  147-148                                150  CH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                    ##STR278##  148-150                                151  CH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                    ##STR279##  143-144                                152  CH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                    ##STR280##  134-135                                153  CH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                    ##STR281##  147-150                                154  CH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                    ##STR282##  148-150                                155  CH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                    ##STR283##  143-145                                156  CH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                    ##STR284##  114-116                                157  CH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                    ##STR285##  125-128                                158  CH.sub.3  CH(CH.sub.3).sub.2                                                                          ##STR286##  95-97                                  159  CH.sub.3  CH(CH.sub.3).sub.2                                                                          ##STR287##  158-160                                160  CH.sub.3  CH(CH.sub.3).sub.2                                                                          ##STR288##  152-153                                161  CH.sub.3  CH(CH.sub.3).sub.2                                                                          ##STR289##  150-152                                162  CH.sub.3  CH(CH.sub.3).sub.2                                                                          ##STR290##  128-130                                163  CH.sub.3  CH(CH.sub.3).sub.2                                                                          ##STR291##  150-152                                164  CH.sub.3                                                                                  ##STR292##                                                                                 ##STR293##  117-118                                165  CH.sub.3                                                                                  ##STR294##                                                                                 ##STR295##  130-132                                166                                                                                  ##STR296##                                                                              C.sub.2 H.sub.5                                                                             ##STR297##  148-150                                167  C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                    ##STR298##  172-173                                168  CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR299##  130-132                                169  CH(CH.sub.3).sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR300##  142-144                                170  (CH.sub.2).sub.3OCH.sub.3                                                                CH.sub.3                                                                                    ##STR301##  127-130                                171  n-C.sub.3 H.sub.7                                                                        C.sub.2 H.sub.5                                                                             ##STR302##  127-130                                172  CH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                    ##STR303##  156-157                                173  CH.sub.3  CH(CH.sub.3).sub.2                                                                          ##STR304##  198-200                                174  CH(CH.sub.3).sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR305##  122-124                                175  (CH.sub.2).sub.3OCH.sub.3                                                                CH.sub.3                                                                                    ##STR306##  97-98                                  176  n-C.sub.3 H.sub.7                                                                        C.sub.2 H.sub.5                                                                             ##STR307##  128-130                                177  CH(CH.sub.3).sub.2                                                                       CH.sub.3                                                                                    ##STR308##  148-150                                178  CH.sub.3  CH(CH.sub.3).sub.2                                                                          ##STR309##  154                                    179  C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                    ##STR310##  145                                    180  CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR311##  134-136                                181  CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR312##  178                                    182  CH.sub.3  n-C.sub.4 H.sub.9                                                                           ##STR313##  142-143                                183  C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                    ##STR314##  115-118                                184  CH.sub.2CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                             ##STR315##  98-99                                  185  CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR316##  114-115 (Na-Salt)                      186  CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR317##  135-140 (Na-Salt)                      187  CH.sub.3  CH.sub.3                                                                                    ##STR318##  161-163 (Na-Salt)                      188  CH.sub.3  C.sub.6 H.sub.5                                                                             ##STR319##  185                                    189  CH.sub.3  C.sub.6 H.sub.5                                                                             ##STR320##  202                                    190  CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR321##  160 (sodium salt)                      191  CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR322##  144 (sodium salt)                      192  C.sub.2 H.sub.5                                                                          CH.sub.3                                                                                    ##STR323##  180 (sodium salt)                      193  CH.sub.3  n-C.sub.4 H.sub.9                                                                           ##STR324##  >270 (sodium salt)                     194  CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR325##  124 (sodium salt)                      195  CH.sub.3  i-C.sub.3 H.sub.7                                                                           ##STR326##  160                                    196  CH.sub.3  i-C.sub.3 H.sub.7                                                                           ##STR327##  167                                    197  CH.sub.3  i-C.sub.3 H.sub.7                                                                           ##STR328##  166                                    198  CH.sub.3  i-C.sub.3 H.sub.7                                                                           ##STR329##  145                                    199  CH.sub.3  i-C.sub.3 H.sub.7                                                                           ##STR330##  126                                    200  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            ##STR331##  113                                    201  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            ##STR332##  102                                    202  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            ##STR333##  103                                    203  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            ##STR334##  114                                    204  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            ##STR335##  105                                    205  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            ##STR336##  135                                    206  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            ##STR337##  147                                    207  CH.sub.3   C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR338##  127                                    208  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            ##STR339##  130                                    209  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            ##STR340##  137                                    210  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            ##STR341##  127                                    211  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            ##STR342##  155                                    212  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            ##STR343##  150                                    213  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR344##  120                                    214  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR345##  109                                    215  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR346##  146                                    216  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR347##  150                                    217  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR348##  170                                    218  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR349##  148                                    219  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR350##  130                                    220  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR351##  110                                    221  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR352##  164                                    222  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR353##  122                                    223  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR354##  92                                     224  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR355##  98                                     225  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR356##  76                                     226  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR357##  88                                     227  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR358##  84                                     228  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR359##  80                                     229  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR360##  76                                     230  CH.sub.3  C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                            ##STR361##  123                                    231  CH.sub.3   C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                           ##STR362##  122                                    232  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR363##  129                                    233  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR364##  132                                    234  CH.sub.3  C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR365##  122                                    235  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR366##  87                                     236  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR367##  78                                     237  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR368##  106                                    238  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR369##  75                                     239  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR370##  80                                     240  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR371##  78                                     241  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR372##  74                                     242  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR373##  78                                     243  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR374##  68                                     244  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 OCH.sub.3                                                                   ##STR375##  98                                     245  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                         ##STR376##  88                                     246  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                         ##STR377##  98                                     247  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                         ##STR378##  106                                    248  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                         ##STR379##  106                                    249  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                         ##STR380##  92                                     250  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                         ##STR381##  136                                    251  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                         ##STR382##  123                                    252  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                         ##STR383##  122                                    253  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                         ##STR384##  116                                    254  CH.sub.3                                                                                  ##STR385##                                                                                 ##STR386##  78                                     255  CH.sub.3  C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                         ##STR387##  126                                    256  CH.sub.3                                                                                  ##STR388##                                                                                 ##STR389##  114                                    257  CH.sub.3                                                                                  ##STR390##                                                                                 ##STR391##  106                                    258  CH.sub.3                                                                                  ##STR392##                                                                                 ##STR393##  107                                    259  CH.sub.3  i-C.sub.3 H.sub.7                                                                           ##STR394##  145 (sodium salt)                      260  CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR395##  140 (sodium salt)                      261  CH.sub.3  C.sub.2 H.sub.5                                                                             ##STR396##  140 (sodium salt)                      262  CH.sub.3                                                                                  ##STR397##                                                                                 ##STR398##  100                                    263  CH.sub.3                                                                                  ##STR399##                                                                                 ##STR400##  99                                     264  CH.sub.3                                                                                  ##STR401##                                                                                 ##STR402##  86                                     265  CH.sub.3                                                                                  ##STR403##                                                                                 ##STR404##  119                                    266  CH.sub.3                                                                                  ##STR405##                                                                                 ##STR406##  119                                    267  CH.sub.3                                                                                  ##STR407##                                                                                 ##STR408##  93                                     268  CH.sub.3                                                                                  ##STR409##                                                                                 ##STR410##  111                                    269  CH.sub.3                                                                                  ##STR411##                                                                                 ##STR412##  113                                    270  CH.sub.3                                                                                  ##STR413##                                                                                 ##STR414##  86                                     271  CH.sub.3                                                                                  ##STR415##                                                                                 ##STR416##  175                                    272  CH.sub.3                                                                                  ##STR417##                                                                                 ##STR418##  90                                     273  CH.sub.3                                                                                  ##STR419##                                                                                 ##STR420##  95                                     274  CH.sub.3                                                                                  ##STR421##                                                                                 ##STR422##  95                                     275  CH.sub.3                                                                                  ##STR423##                                                                                 ##STR424##  130                                    276  CH.sub.3                                                                                  ##STR425##                                                                                 ##STR426##  77                                     277  CH.sub.3                                                                                  ##STR427##                                                                                 ##STR428##  80                                     278  CH.sub.3                                                                                  ##STR429##                                                                                 ##STR430##  92                                     279  CH.sub.3                                                                                  ##STR431##                                                                                 ##STR432##  74                                     280  CH.sub.3                                                                                  ##STR433##                                                                                 ##STR434##  108                                    281  CH.sub.3                                                                                  ##STR435##                                                                                 ##STR436##  112                                    282  CH.sub.3                                                                                  ##STR437##                                                                                 ##STR438##  103                                    283  CH.sub.3  CH.sub.3                                                                                    ##STR439##  127                                    284  CH.sub.3  n-C.sub.3 H.sub.7                                                                           ##STR440##  123                                    285                                                                                  ##STR441##                                                                              n-C.sub.3 H.sub.7                                                                           ##STR442##  128                                    286  CH.sub.3  CH.sub.3                                                                                    ##STR443##  179                                    287  CH.sub.3  CH.sub.3                                                                                    ##STR444##  176                                    288  CH.sub.3  CH.sub.3                                                                                    ##STR445##  178                                    289  CH.sub.3  CH.sub.3                                                                                    ##STR446##  177                                    290                                                                                  ##STR447##                                                                              n-C.sub.3 H.sub.7                                                                           ##STR448##  94                                     291                                                                                  ##STR449##                                                                              n-C.sub.3 H.sub.7                                                                           ##STR450##  115                                    292                                                                                  ##STR451##                                                                              n-C.sub.3 H.sub.7                                                                           ##STR452##  115                                    293                                                                                  ##STR453##                                                                              n-C.sub.3 H.sub.7                                                                           ##STR454##  119                                    294  CH.sub.3  CH.sub.3                                                                                    ##STR455##  170 (sodium salt)                      295  CH.sub.3  CH.sub.3                                                                                    ##STR456##  166                                    296  CH.sub.3  n-C.sub.3 H.sub.7                                                                           ##STR457##  124                                    297  CH.sub.3  n-C.sub.3 H.sub.7                                                                           ##STR458##  178 (sodium salt)                      298  CH.sub.3  CH.sub.3                                                                                    ##STR459##  192                                    299  CH.sub.3  CH.sub.3                                                                                    ##STR460##  160                                    300  CH.sub.3  n-C.sub.3 H.sub.7                                                                           ##STR461##  149                                    301  CH.sub.3  n-C.sub.3 H.sub.7                                                                           ##STR462##  131                                    302  CH.sub.3  n-C.sub.3 H.sub.7                                                                           ##STR463##  156                                    303  CH.sub.3  n-C.sub.3 H.sub.7                                                                           ##STR464##  131                                    304  CH.sub.3  n-C.sub.3 H.sub.7                                                                           ##STR465##  150                                    305  CH.sub.3  n-C.sub.3 H.sub.7                                                                           ##STR466##  171                                    306  CH.sub.3  n-C.sub.3 H.sub.7                                                                           ##STR467##  147                                    307  CH.sub.3  n-C.sub.3 H.sub.7                                                                           ##STR468##  111                                    308  CH.sub.3  n-C.sub.3 H.sub.7                                                                           ##STR469##  124                                    309  CH.sub.3  n-C.sub.3 H.sub.7                                                                           ##STR470##  112                                    310                                                                                  ##STR471##                                                                              n-C.sub.3 H.sub. 7                                                                          ##STR472##  118                                    311                                                                                  ##STR473##                                                                              n-C.sub.3 H.sub.7                                                                           ##STR474##  116                                    312                                                                                  ##STR475##                                                                              n-C.sub.3 H.sub.7                                                                           ##STR476##  103                                    313                                                                                  ##STR477##                                                                              n-C.sub.3 H.sub.7                                                                           ##STR478##  81                                     314                                                                                  ##STR479##                                                                              n-C.sub.3 H.sub.7                                                                           ##STR480##  114                                    315                                                                                  ##STR481##                                                                              n-C.sub.3 H.sub.7                                                                           ##STR482##  120                                    316                                                                                  ##STR483##                                                                              n-C.sub.3 H.sub.7                                                                           ##STR484##  107                                    317                                                                                  ##STR485##                                                                              n-C.sub.3 H.sub.7                                                                           ##STR486##  143                                    318                                                                                  ##STR487##                                                                              n-C.sub.3 H.sub.7                                                                           ##STR488##  132                                    319  CH.sub.3  CH.sub.3                                                                                    ##STR489##  121 (sodium salt)                      320  CH.sub.3  n-C.sub.3 H.sub.7                                                                           ##STR490##  188 (sodium salt)                      321  CH.sub.3  CH.sub.3                                                                                    ##STR491##  175 (sodium salt)                      322                                                                                  ##STR492##                                                                              n-C.sub.3 H.sub.7                                                                           ##STR493##  111                                    323  CH.sub.3                                                                                  ##STR494##                                                                                 ##STR495##  108                                    324  CH.sub.3  i-C.sub.4 H.sub.9                                                                           ##STR496##  129                                    325  CH.sub.3                                                                                  ##STR497##                                                                                 ##STR498##  117                                    326  CH.sub.3  i-C.sub.4 H.sub.9                                                                           ##STR499##  96                                     327  CH.sub.3  CH.sub.2 CF.sub.3                                                                           ##STR500##                                         __________________________________________________________________________

Starting Substances of the Formula (II)

Example (II-1) ##STR501##

A mixture of 5.0 g (0.02 mol) of 1-phenoxycarbonyl-4-allyl-O-methyl-isosemicarbazide and 30 ml of toluene is refluxed for 15 minutes and subsequently concentrated under a water pump vacuum. The residue is triturated with diethyl ether/petroleum ether, and the product which has been obtained in crystalline form is isolated by filtration with suction.

2.0 g (64% of theory) of 4-allyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 111° C. are obtained.

Example (II-2) ##STR502##

50.2 g (0.33 mol) of phenyl hydrazinoformate and 36.6 g (0.33 mol, 93% strength) of trimethyl iminocarbonate are heated to 60° C. in 100 ml of absolute o-dichlorobenzene, and the mixture is stirred for 2 hours, during which process a clear solution is formed. In the course of two hours, it is heated to 120° C., during which process methanol distilled off. A vacuum is applied carefully, during which process more methanol and finally phenol distil off. Further distillation results in a fraction which solidifies in the receiving vessel in crystalline form.

After recrystallisation from toluene, 7.0 g (0.054 mol, 16% of theory) of 4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one of melting point 142°-144° C. are obtained in the form of colourless crystals.

Other examples of compounds of the formula (II) which can be prepared analogously to Examples (II-1) and (II-2) are those listed in Table 4 below.

                  TABLE 4                                                          ______________________________________                                         Examples of the starting substances of the                                     formula (II)                                                                    ##STR503##                   (II)                                             Ex-                                                                            ample                             Melting                                      No.   R.sup.1      R.sup.2        point (°C.)                           ______________________________________                                         II-3  CH.sub.3                                                                                     ##STR504##    163                                          II-4  CH.sub.3     C.sub.3 H.sub.7                                                                                72                                          II-5                                                                                  ##STR505##  CH.sub.3       149                                          II-6                                                                                  ##STR506##  C.sub.2 H.sub.5                                                                               130                                          II-7  CH(CH.sub.3).sub.2                                                                          CH.sub.3       80-81                                        II-8  C.sub.2 H.sub.5                                                                             CH.sub.3       (b.p.: 120° C.                                                          at 1.5 mbar)                                 II-9  C.sub.3 H.sub.7                                                                             CH.sub.3       (b.p.:                                                                         130-150° C.                                                             at 1.5 mbar)                                 II-10 CH.sub.3     C.sub.4 H.sub.9                                                                               152-153                                      II-11 (CH.sub.2).sub.3 OCH.sub.3                                                                  CH.sub.3       84-85                                        II-12 CH.sub.3     C.sub.2 H.sub.5                                                                               (b.p.:                                                                         140-150° C.                                                             at 1.5 mbar)                                 II-13 CH(CH.sub.3).sub.2                                                                          C.sub.2 H.sub.5                                                                               66-67                                        II-14 C.sub.3 H.sub.7                                                                             C.sub.2 H.sub.5                                                                               (b.p.:                                                                         140-150° C.                                                             at 1.5 mbar)                                 II-15 CH.sub.2CHCH.sub.2                                                                          C.sub.2 H.sub.5                                                                               (b.p.: 150° C.                                                          at 1.5 mbar)                                 II-16                                                                                 ##STR507##  n-C.sub.3 H.sub.7                                                                             100                                          II-17 CH.sub.3                                                                                     ##STR508##    106                                          II-18 CH.sub.3     i-C.sub.3 H.sub.7                                                                             134                                          II-19 CH.sub.3     C.sub.2 H.sub.4 OC.sub.2 H.sub.5                                                               90                                          II-20 CH.sub.3     C.sub.2 H.sub.4 OCH.sub.3                                                                     125                                          II-21 C.sub.2 H.sub.5                                                                             C.sub.2 H.sub.4 OCH.sub.3                                                                      94                                          II-22 C.sub.2 H.sub.5                                                                             C.sub.2 H.sub.4 OC.sub.3 H.sub.7 -i                                                            92                                          II-23 CH.sub.3                                                                                     ##STR509##     73                                          II-24 CH.sub.3                                                                                     ##STR510##    (Oil)                                        II-25 CH.sub.3                                                                                     ##STR511##    (Oil)                                        II-26 CH.sub.3                                                                                     ##STR512##     37                                          II-27 CH.sub.3     CH.sub.2 CH(CH.sub.3).sub.2                                                                   (amorphous)                                  II-28 CH.sub.3     CH.sub.2 CHCH.sub.2                                                                            69                                          II-29 CH.sub.3     CH.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                           82                                          II-30 CH.sub.3                                                                                     ##STR513##    116                                          II-31 CH.sub.3     CH.sub.2 C(CH.sub.3).sub.3                                                                    130                                          ______________________________________                                    

Intermediates of the Formula (IX)

Example (IX-1) ##STR514##

A mixture of 30.4 g (0.2 mol) of phenyl hydrazinoformate, 26.0 g (0.2 mol) of methyl N-allyl-iminocarbonate and 150 ml of methanol is stirred for 12 hours at 20° C. and subsequently concentrated under a water pump vacuum. The residue is triturated with diethyl ether/ethanol (1/1 by vol.), and the crystalline product is isolated by filtration with suction.

11.0 g (22% of theory) of 1-phenoxycarbonyl-4-allyl-O-methyl-isosemicarbazide of melting point 114° C. are obtained.

Other examples of compounds of the formula (IX) which can be prepared analogously to Example (IX-1) are those listed in Table 5 below.

                  TABLE 5                                                          ______________________________________                                         Examples of the compounds of the formula (IX)                                   ##STR515##                   (IX)                                             Example                            Melting                                     No.       R.sup.1                                                                               R.sup.2  R.sup.4  point (°C.)                          ______________________________________                                         IX-2      CH.sub.3                                                                              CH.sub.3                                                                                 ##STR516##                                                                             123                                         IX-3      C.sub.2 H.sub.5                                                                       CH.sub.3 C.sub.2 H.sub.5                                                                         137                                         IX-4      CH.sub.3                                                                              CH.sub.3 CH.sub.3 134                                         IX-5      CH.sub.3                                                                              CH.sub.3 C.sub.2 H.sub.5                                                                         135                                         IX-6      C.sub.2 H.sub.5                                                                       CH.sub.3                                                                                 ##STR517##                                                                             133-134                                     ______________________________________                                    

Use Examples

In the Use Examples, the following compound (A) is used as comparison substance: ##STR518##

2-(2-chloro-phenylsulphonylaminocarbonyl)-4,5-dimethyl-2,4-dihydro-3H-1,2,4-triazol-3-one (disclosed in EP-A 341,489).

Example A

Post-emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Test plants-which have a height of 5-15 cm are sprayed with the preparation of the active compound in such a way as-to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is so chosen that the particular amounts of active compound desired are applied in 1,000 l of water/ha. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote:

0%=no action (like untreated control)

100%=total destruction

In this test, a considerably more powerful action against weeds than the known compound (A) is shown, for example, by the compounds of Preparation Examples 1, 2, 3, 53, 54, 55, 56, 57, 58, 64, 65 and 67, while having, in some cases, good crop plant compatibility.

Example B

Pre-emergence Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil and, after 24 hours, watered with the preparation of the active compound. It is expedient to keep constant the amount of water per unit area. The concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive. After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote:

0%=no action (like untreated control)

100%=total destruction

In this test, a considerably more powerful action against weeds than the known compound (A) is shown, for example, by the compounds of Preparation Examples 2, 54 and 69, while having, in some cases, good crop plant compatibility.

It will be understood that the specification and examples are illustrative but not imitative of the present invention and that other embodiments within the spirit and scope of the invention will suggest themselves to those skilled in the art. 

We claim:
 1. A sulphonylaminocarbonyltriazolinone of the formula ##STR519## in which R¹ represents hydrogen; methyl optionally substituted by fluorine, chlorine, cyano or C₁ -C₄ -alkoxy; or cyclopropyl;R² represents C₁ -C₆ -alkyl optionally substituted by fluorine, chlorine, C₃ -C₆ -cycloalkyl or C₁ -C₄ -alkoxy; C₃ -C₆ -alkenyl optionally substituted by at least one of fluorine, chlorine and bromine; C₃ -C₆ -alkinyl; C₃ -C₆ -cycloalkyl; phenyl; or fluorophenyl, R³ represents the group ##STR520## in which R⁴ and R⁵ are identical or different and represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, C₁ -C₆ -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylaminocarbonyl, di-(C₁ -C₄ -alkyl ) amino-carbonyl, hydroxyl, C₁ -C₄ -alkoxy, formyloxy, C₁ -C₄ -alkyl-carbonyloxy, C₁ -C₄ -alkoxy-carbonyloxy, C₁ -C₄ -alkylamino-carbonyloxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, di-(C₁ -C₄ -alkyl)-aminosulphonyl, C₃ -C₆ -cycloalkyl or phenyl), or represent C₂ -C₆ -alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl), or represent C₂ -C₆ -alkinyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl), or represent C₁ -C₄ -alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl), or represent C₁ -C₄ -alkylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl), or represent C₃ -C₆ -alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C₁ -C₄ -alkoxy-carbonyl), or represent C₂ -C₆ -alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₃ -alkylthio or C₁ -C₄ -alkoxycarbonyl), C₃ -C₆ -alkinyloxy, C₃ -C₆ -alkinylthlo or the radical --S(O)_(p) --R⁶ where P represents the numbers 1 or 2 and R⁶ represents C₁ -C₄ -alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano or C₁ -C₄ -alkoxy-carbonyl), C₃ -C₆ -alkenyl, C₃ -C₆ -alkinyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkoxy-C₁ -C₄ -alkylamino, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)-amine, phenyl or the radical --NHOR⁷ where R⁷ represents C_(1l) -C₁₂ -alkyl (which is optionally substituted by fluorine, chlorine, cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio. C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, C₁ -C₄ -alkyl-carbonyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkylamino-carbonyl or di-(C₁ -C₄ -alkyl)-amino-carbonyl), or represents C₃ -C₆ -alkenyl (which is optionally substituted by fluorine, chlorine or bromine), C₃ -C₆ -alkinyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₂ -alkyl, phenyl-C₁ -C₂ -alkyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxy-carbonyl), or represents benzhydryl, or represents phenyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, c₁ -c₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy, C₁ -C₄ -fluoroalkoxy, C₁ -C₄ -alkylthio, trifluoromethylthio or C₁ -c₄ -alkoxy-carbonyl), R⁴ and/or R⁵ furthermore represent phenyl or phenoxy, or represent C₁ -C₄ -alkylcarbonylamino, C₁ -C₄ -alkoxycarbonylamino, C₁ -C₄ -alkylamino-carbonyl-amino, di-(C₁ -C₄ -alkyl)-amino-carbonylamino, or the radical --CO--R⁸ whereR⁸ represents C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₃ -C₆ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylamino, C₁ -C₄ -alkoxyamino, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl-amino or di-(C₁ -C₄ -alkyl)-amino (which are optionally substituted by fluorine and/or chlorine), R⁴ and/or R⁵ furthermore represent trimethylsilyl, C₁ -C₄ -alkylsulphonyl, di-(C₁ -C₄ -alkyl)-aminosulphonylamino or the radical --CH═N--R⁹ where R⁹ represents C₁ -C₆ -alkyl which is optionally substituted by fluorine, chlorine, cyano, carboxyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl, or represents benzyl which is optionally substituted by fluorine or chlorine, or represents C₃ -C₆ -alkenyl or C₃ -C₆ -alkinyl, each of which is optionally substituted by fluorine or chlorine, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio, or represents optionally fluorine- and/or chlorine-substituted C₁ -c₆ -alkoxy, C₃ -C₆ -alkenoxy, C₃ -C₆ -alkinoxy or benzyloxy, or represents amino, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)-amino, phenylamino. C₁ -C₄ -alkyl-carbonyl-amino, C₁ -C₄ -alkoxycarbonylamino or C₁ -C₄ -alkyl-sulphonylamino, or represents phenylsulphonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl,furthermore R³ represents the radical ##STR521## where R¹⁰ represents hydrogen or C₁ -C₄ -alkyl,R¹¹ and R¹² are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine), C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine), carboxyl, C₁ -C₄ -alkoxy-carbonyl, dimethylaminocarbonyl, C₁ -C₄ -alkylsulphonyl or di-(C₁ -c₄ -alkyl)aminosulphonyl;furthermore R³ represents the radical ##STR522## where R¹³ and R¹⁴ are identical or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl (which is optionally substituted by fluorine and/or chlorine) or C₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/or chlorine)or a salt thereof, with the exception of the compounds: 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one, and 2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-cyclopropyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one.
 2. A sulphonylaminocarbonyl-triazolinone or salt thereof according to claim 1, in whichR¹ represents hydrogen, methyl which is optionally substituted by fluorine, cyano, methoxy or ethoxy, or represents cyclopropyl, R² represents C₁ -C₄ -alkyl which is optionally substituted by fluorine and/or chlorine, methoxy or ethoxy, or represents C₃ -C₄ -alkenyl which is optionally substituted by fluorine and/or chlorine, or represents C₃ -C₆ -cycloalkyl, and R³ represents the group ##STR523## where R⁴ represents fluorine, chlorine, bromine, methyl trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, 2-chloro-ethoxy, 2-methoxy-ethoxy, C₁ -C₃ -alkylthio, C₁ -C₃ -alkylsulphinyl, C₁ -C₃ -alkylsulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylaminosulphonyl, methoxyaminosulphonyl, phenyl, phenoxy or C₁ -C₃ -alkoxy-carbonyl and R⁵ represents hydrogen, fluorine, chlorine or bromine;furthermore R³ represent the radical ##STR524## where R¹⁰ represents hydrogen,R¹¹ represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl and R¹² represents hydrogen;with the exception of the compounds: 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one, and 2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-cyclopropyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one.
 3. A sulphonylaminocarbonyltriazolinone or salt thereof according to claim 1, in whichR¹ represents methyl or cyclopropyl, R² represents C₁ -C₆ -alkyl or phenyl, and R³ represents ##STR525## , in which R⁴ represents chlorine, bromine, methyl optionally substituted by fluorine, methoxy which is substituted by fluorine or the radical --COOCH₃, and R⁵ represents hydrogen or methyl, with the exception of the compounds: 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one, and 2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-cyclopropyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one.
 4. A compound or salt thereof according to claim 3, wherein the compound is selected from the group consisting of those of the following table:

    ______________________________________                                         --R.sup.1   --R.sup.2  --R.sup.4   --R.sup.5                                   ______________________________________                                         CH.sub.3    --C.sub.2 H.sub.5                                                                         COOCH.sub.3 H                                           CH.sub.3    --C.sub.3 H.sub.7 -n                                                                      COOCH.sub.3 H                                           CH.sub.3    --C.sub.3 H.sub.7 -i                                                                      COOCH.sub.3 H                                           Cyclopropyl --C.sub.2 H.sub.5                                                                         OCHF.sub.2  H                                           Cyclopropyl --C.sub.3 H.sub.7 -n                                                                      OCF.sub.3   H                                           CH.sub.3    CH.sub.3   OCF.sub.3   H                                           Cyclopropyl C.sub.2 H.sub.5                                                                           COOCH.sub.3 H                                           CH.sub.3    C.sub.6 H.sub.5                                                                           CH.sub.3    H                                           CH.sub.3    C.sub.6 H.sub.5                                                                           COOCH.sub.3 H                                           CH.sub.3    C.sub.6 H.sub.5                                                                           Cl          6-CH.sub.3                                  CH.sub.3    C.sub.6 H.sub.5                                                                           OCF.sub.3   H                                           CH.sub.3    C.sub.6 H.sub.5                                                                           Br          H                                           CH.sub.3    CH.sub.3   CH.sub.3    H                                           CH.sub.3    CH.sub.3   Br          H                                           CH.sub.3    CH.sub.3   Cl          6-CH.sub.3                                  CH.sub.3    CH.sub.3   CF.sub.3    H                                           CH.sub.3    C.sub.6 H.sub.5                                                                           CF.sub.3    H                                           CH.sub.3    C.sub.2 H.sub.5                                                                           OCF.sub.3   H                                           CH.sub.3    C.sub.2 H.sub.5                                                                           CF.sub.3    H                                           CH.sub.3    CH.sub.3   OCHF.sub.2  H                                           Cyclopropyl C.sub.2 H.sub.5                                                                           Br          H                                           Cyclopropyl C.sub.2 H.sub.5                                                                           Cl          H                                           Cyclopropyl C.sub.2 H.sub.5                                                                           Cl          6-CH.sub.3                                  CH.sub.3    C.sub.2 H.sub.5                                                                           Cl          H                                           CH.sub.3    C.sub.2 H.sub.5                                                                           Cl          6-CH.sub.3                                  ______________________________________                                    


5. A compound or salt thereof according to claim 3, wherein R⁵ represents hydrogen and the compound is selected from the group consisting of those of the following table:

    ______________________________________                                         --R.sup.1       --R.sup.2   --R.sup.4                                          ______________________________________                                         CH.sub.3        --C.sub.2 H.sub.5                                                                          COOCH.sub.3                                        CH.sub.3        C.sub.3 H.sub.7 -n                                                                         COOCH.sub.3                                        CH.sub.3        C.sub.3 H.sub.7 -i                                                                         COOCH.sub.3                                        CH.sub.3        --CH.sub.3  --OCF.sub.3                                        CH.sub.3        --C.sub.2 H.sub.5                                                                          --OCF.sub.3                                        CH.sub.3        --C.sub.3 H.sub.7 -n                                                                       --OCF.sub.3                                        CH.sub.3        --C.sub.3 H.sub.7 -i                                                                       --OCF.sub.3                                        CH.sub.3        --CH.sub.3  --CF.sub.3                                         CH.sub.3        --C.sub.2 H.sub.5                                                                          --CF.sub.3                                         CH.sub.3        --C.sub.3 H.sub.7 -n                                                                       --CF.sub.3                                         CH.sub.3        --C.sub.3 H.sub.7 -i                                                                       --CF.sub.3                                         Cyclopropyl     --C.sub.2 H.sub.5                                                                          COOCH.sub.3                                        Cyclopropyl     --C.sub.3 H.sub.7 -n                                                                       COOCH.sub.3                                        Cyclopropyl     --C.sub.2 H.sub.5                                                                          --OCF.sub.3                                        Cyclopropyl     --C.sub.3 H.sub.7 -n                                                                       --OCF.sub.3                                        Cyclopropyl     --CH.sub.3  --CF.sub.3                                         Cyclopropyl     --C.sub.2 H.sub.5                                                                          --CF.sub.3                                         Cyclopropyl     --C.sub.3 H.sub.7 -n                                                                       --CF.sub.3                                         ______________________________________                                    


6. A compound or salt thereof according to claim 1, wherein such compound is ##STR526##
 7. A compound or salt thereof according to claim 1, wherein such compound is ##STR527##
 8. A compound or salt thereof according to claim 1, wherein such compound is ##STR528##
 9. A compound or salt thereof according to claim 2, wherein such compound is ##STR529##
 10. A compound or salt thereof according to claim 1, wherein such compound is ##STR530##
 11. A compound or salt thereof according to claim 1, wherein such compound is ##STR531##
 12. A compound or salt thereof according to claim 1, wherein such compound is ##STR532##
 13. A compound or salt thereof according to claim 1, wherein such compound is ##STR533##
 14. A compound or salt thereof according to claim 1, wherein such compound is ##STR534##
 15. A compound or salt thereof according to claim 1, wherein such compound is ##STR535##
 16. A compound or salt thereof according to claim 1, wherein such compound is ##STR536##
 17. A compound or salt thereof according to claim 1, wherein such compound is ##STR537##
 18. A herbicidal composition comprising a herbicidally effective amount of a compound or salt thereof according to claim 1 and a diluent.
 19. A method of combatting unwanted vegetation which comprises applying to such vegetation or to a locus from which it is desired to exclude such vegetation a herbicidally effective amount of a compound or salt thereof according to claim
 1. 20. A method of combatting unwanted vegetation which comprises applying to such vegetation or to a locus from which it is desired to exclude such vegetation a herbicidally effective amount of a compound or salt thereof according to claim
 4. 